The rapper and producer Big Boi has sold over 50 million records as a solo artist and as half of the platinum-selling hip hop duo OutKast. The innovative Atlanta-based group broke out in the mid-1990s with "Rosa Parks" and "Elevators", then followed up with crossover pop hits like "The Way You Move" and "Bombs Over Baghdad".

OutKast found huge commercial success with an experimental brand of hip hop, eschewing old-school samples in favor of new sounds. Big Boi has been the more musically prolific member of the group. He's gone on to produce several solo albums and collaborate with artists across the music spectrum, from fellow ATL-based rapper Ludacris to funk-master George Clinton to the indie rock band Wavves.

Big Boi joins us to talk about the early days recording in a clay-walled basement, coming to terms with fame, and where to go musically when you've hit monumental commercial success.

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Catherine O'Hara on Being Slightly, Perfectly Odd

Catherine O'Hara's work embodies a particularly special brand of comic absurdity. She helped launch SCTV alongside other burgeoning comedy greats like John Candy and Eugene Levy, quit the show, but still moved on to star in blockbuster comedies. She became spiritually possessed in Beetlejuice, played a memorable, anxiety-ridden mother to Macaulay Culkin in Home Alone, and became a critical part of Christopher Guest's ensemble mockumentaries, like Waiting for Guffman and Best in Show.

O'Hara talks to us about the difficulties of being a woman in the SCTV writers' room, creating memorable characters with her longtime friend and collaborator Eugene Levy, and her own secret comedic formula.

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The Outshot: Fast, Cheap, and Out Of Control

At first, Errol Morris's documentary Fast, Cheap & Out of Control looks like it's about four men and their professional occupations: a lion tamer, a topiarist, a roboticist, a scientist who studies naked mole rats. But the movie is about much more than just weird jobs.

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When Captain Picard falls for a pointy coworker, the harmony of their relationship reverberates throughout the ship. But when things heat up on a nearby planet, Picard must make a choice between saving some lives and extinguishing their romance. What's the least Kevin-y impression? Is the Hood the only place you can be truly safe? Who's had the worst life on the show? It's the episode with a decidedly non-Naked Gun love story.

Comedian and author Greg Behrendt joins Jordan and Jesse as they take a break from analyzing the polls to have a fun week, you know, just for them. They get into Greg's early morning bike rides, Jesse's mom's new potential roommate who is both a bouncer and an EMT, and the important question of how much you should spend on eunuchs for a media empire.

Biz and Theresa are beginning to think we aren’t using the word "selfish" right. Wanting time for yourself so you can rest isn’t the same thing as shoving someone out of the lifeboat. As we find ourselves digging into the idea of self-care more and more on the show, we try to figure out this week why it's hard to allow ourselves our own wants and desires. Plus Biz has an unimportant update, Theresa is getting messages and they're coming from within her bra, and we talk to Brett McKay about his book, The Art of Manliness, which, as it turns out, is helpful to parents and non-parents, regardless of gender!

In this episode of Dead Pilots Society, Ben Blacker interviews Samantha McIntyre (Married, Bored to Death) regarding her dead pilot, Rollerworld. You'll also listen to a never-before-heard live table read of Rollerworld performed by some of today's funniest comedic actors.

This week's episode of The Bachelorette featured a lot of fun dates and a lot of super-not-fun horseshit back at the mansion. Not literal horse shit, mind you -- we all know this franchise is too afraid to actually deliver on THOSE goods.

When the Entrepreneur is getting sprayed for space bugs, the entire crew disembarks for a local planet famous for its incessant smalltalk and picturesque horse riding trails. But when a ruthless group of criminals try to steal the nastiest stuff that comes out of the ship’s reactor, only JL Pipes can stop them. How often do the ship’s flight attendants have to do a brief safety demonstration? What other ‘hand stuff’ did Picard learn from Sarek? Is this just Wars trying to pull a heist on Trek? It’s the episode where chattiness is punishable by death.

Kathryn Hahn is an actor and has been in comedy films like Step Brothers, the Anchorman movies, and a bunch more. She's also starred in the NBC series Crossing Jordan and was also on Parks and Recreation, playing Jennifer Barkley, the political consultant.

Lately, she's been working a lot with the writer and director Jill Soloway. She was in her 2013 film Afternoon Delight, she plays Raquel the rabbi on Amazon's Transparent, and now she's starring in another Amazon series called I Love Dick, based on the Chris Klaus book by the same name.

Hahn and Jesse talk about the inherently feminist space that I Love Dick inhabits, and the deeply complex character that Kathryn plays on the show. She talks about working with Jill Soloway on many of her most recent projects, and the special and deeply creative environment that Soloway creates on her sets.

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Jason Zinoman on "The Last Giant of Late Night", David Letterman

Jason Zinoman is a writer and a critic covering comedy over at the New York Times. He also writes for Slate and Vanity Fair. He's got a new book out - it's called Letterman: The Last Giant of Late Night. More than a biography of David Letterman, it is about one of the funniest TV hosts of all time and why so many people are fascinated with him.

Jason and Jesse talk about the span of David Letterman's career, from parodying regional radio on his college radio station, to his time working as the weekend television weatherman, to his late night show segments that appealed to really basic comedic instincts in the audience (i.e. "Dropping Stuff off a 5 Story Tower" and "Stupid Pet Tricks" and "How many Guys in Spider-Man Suits Can Fit Into a Jamba Juice").

Sorry it's come down to this, dear listeners, but we've been cops the whole time, and we've got to take you down for all the crimes you did while enjoying our podcast. We'd still love to have you over for the big cookout next weekend, though!

Comedian and podcaster Danielle Radford joins Jordan and Jesse and they finally give it a rest from talking about those clowns in Washington to make room for a discussion about everyone's favorite Reddit subculture, movies that are better to watch on VHS than Blu-ray and the mystery of those fried baby squid that come with calamari.